| Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines. | |
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MedLine Citation:
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PMID: 15255724 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A novel and efficient synthesis of the pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine system, the heterocyclic core of the variolin family of marine alkaloids, is described. The route involves the reaction of 3-bromo-2-(bromomethyl)pyrrolo[2,3-b]pyridine and tosylmethyl isocyanide (TosMIC) under phase-transfer conditions. This unprecedented reaction was also used to synthesize a series of new methoxycarbonyl azolopyrimidines by reaction of TosMIC with bromomethylindoles, bromomethylbenzimidazole, and bromomethylpyrazole. Hydrolysis and decarboxylation of 5-bromo-7-methoxycarbonylpyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine obtained by this heterocyclization process and installation of the pyrimidine moiety in the C5 position open an alternative approach to complete a total synthesis of variolin B. |
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Authors:
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Javier Mendiola; Alejandro Baeza; Julio Alvarez-Builla; Juan J Vaquero |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Jul |
Date Detail:
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Created Date: 2004-07-16 Completed Date: 2004-09-17 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4974-83 Citation Subset: IM |
Affiliation:
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Departamento de Química Orgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkaloids
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chemical synthesis*,
chemistry Animals Azoles / chemistry* Cyanides / chemistry* Cyclization Molecular Structure Porifera / chemistry Pyrimidines / chemical synthesis*, chemistry Tosyl Compounds / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Alkaloids; 0/Azoles; 0/Cyanides; 0/Pyrimidines; 0/Tosyl Compounds |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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